Methyl iodide → HCID 60198853, compound

Participants

Reaction Steps

A suspension of PS—PPh3 (278 mg, 2.28 mmol/g, 0.634 mmol) and THF (5 mL) was was allowed to stand for 5 min then a solution 332 (136 mg, 0.317 mmol) in THF (1 mL) was added. The suspension was stirred at RT for 4 h then MeI (0.0593 mL, 0.951 mmol) was added. The mixture was stirred at RT for 17 h, filtered through a fritted funnel and the resin washed with THF (5×10 mL) and DCM (5×10 mL). The resin was transferred to a pressure tube and suspended in MeOH (8 mL) and a solution of KOH (178 mg, 3.17 mmol) in MeOH (2 mL) was added. The mixture was heated to 65° C. for 4 h, cooled to RT, filtered and the resin washed with DCM (4×3 mL) and MeOH (2×3 mL). The filtrate and washings were combined and concentrated to a white solid. The crude product was partitioned between DCM and dilute aq. NaHCO3 and the aqueous layer extracted with EtOAc. The combined organic extracts were dried (MgSO4), filtered, and concentrated. The crude product was purified on a preparative TLC plate (0.5 mm) developed with MeOH/DCM/NH4OH (9/90/1) to afford 50 mg (38%) of I-117 as a pale yellow foam: 1H NMR (400 MHz, CDCl3) δ 8.06 (s, 1H), 7.72 (br s, 1H), 7.22-7.28 (m, 4H), 4.95 (m, 1H), 4.80 (d, 1H), 4.37 (m, 2H), 4.10 (m, 1H), 3.69 (m, 1H), 3.60 (m, 1H), 2.72 (m, 2H), 2.65 (t, 2H), 2.48 (s, 3H), 2.05 (m, 1H), 1.80 (m, 1H), 1.22 (d, 6H); LRMS (APCI pos) m/e=417.4 (M+H).

Provenance & Evidence